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Preheat your oven to 350 degrees F. Spread the coconut on a baking sheet and bake for 8 to 10 minutes, stirring once halfway through, or until the coconut is mostly golden brown. Let it cool, then pour it onto a medium plate that is slightly bigger than the rim of your glass.
Pour the simple syrup onto another medium plate. Invert an 18-ounce schooner glass onto the simple syrup so that the rim of the glass gets a coating. Let the excess drip off, then dip the rim of the schooner into the toasted coconut to coat the entire rim of the glass.
Fill the schooner with ice, then add a little bit more ice to a cocktail shaker.
Pour the rum, pina colada mix, and juices into the cocktail shaker. Shake vigorously for 10 seconds, then strain the drink into the schooner glass.
Sprinkle a dash of nutmeg on top of the drink, then use a toothpick to attach the cherry to the rind side of a wedge of fresh pineapple. Cut a slit about halfway up on one side of the pineapple wedge and slide it onto the rim of the glass.
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